|
【结 构 式】 
|
【药物名称】 【化学名称】4-Acetyl-[7-[3-(3,4-dimethoxybenzylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-1,4-benzoxazine 【CA登记号】 【 分 子 式 】C22H28N2O6 【 分 子 量 】416.47826 |
【开发单位】Otsuka (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Hypertension, Treatment of, Positive Inotropic Agents, Vasodilators |
合成路线1
The acylation of 7-hydroxy-3,4-dihydro-2H-1,4-benzoxazine (I) with acetic anhydride gives the N-acetyl derivative (II), which is condensed with epichlorohydrin (III) by means of K2CO3 at 90-5 C yielding 4-acetyl-7-(2,3-epoxypropoxy)-3,4-dihydro-2H-1,4-benzoxazine (IV). Finally, the addition of 3,4-dimethoxybenzylamine (V) to the epoxy group of (IV) in hot isopropanol affords the target compound.
| 【1】 Iakovou, K.; et al.; Synthesis of oxypropanolamine derivatives of 3,4-dihydro-2H-1,4-benzoxazine, beta-adrenergic affinity, inotropic, chronotropic and coronary vasodilating activities. Eur J Med Chem 1999, 34, 11, 903. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 38404 | 3,4-dihydro-2H-1,4-benzoxazin-7-ol | C8H9NO2 | 详情 | 详情 | |
| (II) | 38405 | 1-(7-hydroxy-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-1-ethanone | C10H11NO3 | 详情 | 详情 | |
| (III) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (IV) | 38406 | 1-[7-(2-oxiranylmethoxy)-2,3-dihydro-4H-1,4-benzoxazin-4-yl]-1-ethanone | C13H15NO4 | 详情 | 详情 | |
| (V) | 13920 | (3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine | 5763-61-1 | C9H13NO2 | 详情 | 详情 |
Extended Information